Triethylamine → (S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamate

HRID 651591Notes

Reaction equation

HRID 651591 reaction equation
[C:1]([C@@H](C)C(N)(N)C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[OH:23]C1C2N=NNC=2C=CC=1.Cl.C[N:35]([CH3:44])[CH2:36][CH2:37][CH2:38][N:39]=C=NCC>C1COCC1>[C:4]([O:3][C:1](=[O:2])[NH:39][C@H:38]1[CH2:37][CH2:36][NH:35][C:44]1=[O:23])([CH3:5])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86752309(S)-Boc-Diaminobutyric acidHCID 178418300HCID 178418300, compound

Product 1

HCID 10750535(S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamateYield 85.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

(S)-Boc-Diaminobutyric acid (25 g, 115 mmol), triethylamine (35 g, 344 mmol), and hydroxybenzotriazole (19.3 g, 143 mmol) are dissolved in THF (300 mL). 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (27.4 g, 143 mmol) is added to the solution. The solution is heated to 60° C. over 15 minutes. A white precipitate forms and the solution is kept at 60° C. for 4 hours. After this time, the solution is filtered and the collected liquid is concentrated. The crude product is purified by column chromatography in a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2 to afford the title compound (19.6 g, 98 mmol) as a white solid.

Workup

  1. filtrationAfter this time, the solution is filtered
  2. concentrationthe collected liquid is concentrated
  3. customThe crude product is purified by column chromatography in a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-bb085317b1664684a8d73ec2a9313b52
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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